Reactions of Azides and Alkynes

My group is interested in exploring novel reactions of azides and alkynes. Traditionally, these two components have been assembled to form 1,4-substituted triazoles, one of the “click reactions.” Complementary to this work, our group has determined a method to react alkynes and sulfonyl-azides to form 1,5-sulfonyl-triazoles. The umpolung reactivity was also explored wherein an electrophilic alkyne was reacted with azide nucleophiles to form and react as cyanocarbenes after extrusion of dinitrogen. Funding for this project was provided by the American Chemical Society Petroleum Research Fund in the form of a Doctoral New Investigator (52488-DNI1) and is currently provided by the National Science Foundation in the form of a CAREER grant (1351883). This support is gratefully acknowledged.

Representative Publications:

“Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and Its Reactivity with Aromatic Systems”
Mohammed H. Al-Huniti, Zachary B. Sullivan, Jarrod L. Stanley, James A. Carson, I. F. Dempsey Hyatt, A. Christina Hairston, and Mitchell P. Croatt
Journal of Organic Chemistry 2017, 82, 11772-117780.
(Special Issue for Hypervalent Iodine)

“Formation and in situ reactions of hypervalent iodonium alkynyl triflates to form cyanocarbenes”
I. F. Dempsey Hyatt, Daniel J. Nasrallah, Michael A. Maxwell, A. Christina F. Hairston, Manahil M. Abdalhameed, and Mitchell P. Croatt
Chemical Communications 2015, 51, 5287-5289.!divRelatedContent

“Exploring the reactivity of 1,5-disubstituted sulfonyl-triazoles: Thermolysis and Rh(II)-catalyzed synthesis of α-sulfonyl nitriles”
Maria Elena Meza-Aviña, Mudita Kishor Patel, and Mitchell P. Croatt
Tetrahedron 201369, 7840-7846.
(Special Issue in Honor of Professor Wender)

“Reactions of Hypervalent Iodonium-Alkynyl Triflates with Azides: New Mechanistic Approach for the Generation of Cyanocarbenes”
I. F. Dempsey Hyatt, Mitchell P. Croatt
(Featured with the Front Cover Graphic of that issue of Angew. Chem., Int. Ed. and Highlighted in Angew. Chem. Int. Ed. 201251, 12169-12171.)

“Selective Formation of 1,5-Substituted Sulfonyl Triazoles Using Acetylides and Sulfonyl Azides”
Maria Elena Meza-Aviña, Mudita Kishor Patel, Cylivia B. Lee, Thomas J. Dietz, Mitchell P. Croatt
Organic Letters 2011, 13, 2984-2987; 

(Highlighted in SYNFACTS 2011, 9, 1005)

“Alkynes and Azides:  Not Just for Click Reactions”
I. F. Dempsey Hyatt, Maria Elena Meza-Aviña, and Mitchell P. Croatt
Synlett 2012, 23, 2869-2874.
(Invited SYNPACTS article)